(Jim Mooney, the deputy director of a multistate independent school organization, visited me in South Carolina, and we continued our summer conversation on school leadership.)

As we moved from our discussion on effective communication, Jim plunged right in: “The single biggest complaint I hear about headmasters and heads of school concerns the host of issues around making decisions, rolling them out, and moving forward.”

“Sometimes that’s it,” he said, “but other times a head will make a decision in wrong manner---taking too long or doing so impulsively. Some heads try to make what I would call ‘safe decisions;’ others make decisions that are not carefully thought through, so a decision is greeted with confusion.”

Decision Fatigue or Indecisiveness?

I reflected on this and thought about my own years of Headship: “I found that having constantly to be ‘the decider’ required a good deal of energy and focus.”

“Right,” he said. “I believe the straightforward issue of fatigue is behind a good deal of what seems to be indecision. Once a head of school makes a decision, there usually follows a host of consequential decisions and those take time and energy.”

I recognized this immediately: “Like communication, before and after; then dealing with reactions, follow up, and assessing the outcome of decisions.”

“Talking about it,” Jim laughed, “is fatiguing.”

When I asked him what he thinks are the specific factors behind the decision fatigue issue, he offered three:

The sheer number of decisions and the daily demand for decision-making, large and small; in the daily life of school management

The process of meeting with people, groups, individuals around many of the decisions

The preparation, research, and follow through necessary to make informed strategic decisions that have a successful outcome

“Ideally, yes,” said Jim, “but my experience suggests that delegation only means a head is brought into the process at a different point, not very often is the head removed from the flow of decisions moving through the community.”

“So,” I said, “given the relentless demand for decisive action, sometimes a headmaster will lapse into an indecisive mode almost as a restorative process?”

“Let’s say,” Jim said, “that understanding the daily energy necessary to be a successful head of school requires managing the decision-making process as a top priority.”

“And,” I followed up, “avoiding the ‘indecisive’ reputation has to do with maintaining pro-active energy as much as possible.”

Jim agreed: “Heads need what I would call ‘a ventilation plan,’ someone with whom to blow off the inevitable frustrations that arise when managing the decision-making process. A trusted colleague, a close trustee, even a spouse, but having that ‘release valve” is key.”

Decider versus Pleaser

“Do you think,” I asked, “that headmasters do not like to make tough decisions because they value—too highly, I guess—their popularity?”

Jim thought a minute. “That’s not quite it. I think that heads of school are invariably people who try to please various groups, and frankly are good at doing so. However, whenever a head confronts an especially tough decision—and sometimes it feels like every decision is tough—the head knows that no matter what the choices made will invariably not only fail to please but actually upset people. Generally speaking, heads do not like to do that.”

“Sure,” I said, “but remember, as we have discussed, a school community wants to be led by a person they respect, not always someone they like. And to gain respect, a headmaster has to care a lot less about being the pleaser, and perhaps more about being the decider.”

Jim followed. “First, a head of school has to accept that some people—faculty members, parents, even a trustee or two—may never warm to her or him for unknown reasons and the best one can hope for is acceptance.”

“ In other words,” I said, “devalue all the pleasing behavior.”

“Well,” said Jim, “not entirely, but do not put pleasing people ahead of making tough decisions. Heads need to lead, even push forward sometimes toward clear outcomes. I think doing so will allow the majority of the stakeholders to respect the work of the head and appreciate the leadership. In other words, take the ‘please like me’ issue off the table, and put the assessment and value of ‘here is what we are doing’ and ‘we are going here’ on the table.”

“And,” I asked, “the ‘what we are doing’ is generally about decision-making?”

“Yes,” Jim said, “but it is that and all the other stuff: communication, inclusion, transparency, and so on. In the end, heads are usually judged on how well they handle decision-making, even though many decisions are made with significant uncertainty about the outcome. Not all that many decisions are proven right or wrong by the end of the week.”

“Like what?” I asked.

“That list is long,” Jim answered, “but certainly hiring and promoting people are in that category because the community gets to judge how the person does; if a head decides to keep a problematic student, there can be a positive or negative outcome; trying anything new—a schedule, grading system, calendar, and so on—can be a great move or a mess. Still, there are always decisions to be made, and there are always groups of people on either side of almost every decision, ready to point out how wrong it is even before an outcome is clear.”

“Here’s an example,” I offered. “Say a significant position opens up—it could be anything—but the key is that the position is a step up and there are a number of seasoned, senior people expecting to be considered for the appointment. However, as head of school, you intuitively believe that a less seasoned but impressive ‘natural leader’ is the key person to rise in your community and provide an essential quality your team may presently lack—could be perspective, courage, energy, whatever. To you and a few others, this person has that essence of ability you think the school needs, and none of the other candidates—who are popular and may have qualities in their own right—has the breadth of talent or potential that this ‘natural leader’ does.”

Just Do It: Courage and Ownership

“Okay,” said Jim, “I see where you are going. Does the head have the courage to face the howls of protest and unhappiness by going with the less experienced person?”

“And of course,” I followed, “the success or failure in such a decision may not be certain for years to come, but the criticism of the decision will linger on.”

Jim said, “That reality is true of many, many decisions. In this example, a head would likely have to endure second-guessing, resentment from the spurned candidates, and initial unhappiness from the other candidates’ friends And in the ‘no good deed goes unpunished category’ even the person who is elevated may feel the appointment is harmful to his or her popularity—and blame the head. Still, if the decision is correct—which it might not be—the rewards could be very high.”

“Given the scenario,” I asked, “is there a right decision?”

“That isn’t the point. The important factor is that the headmaster “own” the decision, and not be twisted in knots of indecisiveness. In short, the head of school sees the decision for what it is, assesses the risks, weighs the rewards, understands the goals and seeks to assure a good outcome.”

“ Then make the decision.”

“Yes. Make it and act upon it. Communicate the decision thoughtfully and with sensitivity to all concerned…these sort of decisions—and there are hundreds each year—are the kind that toughen the skin of a head of school.”

And I agree with Jim. Regardless of how good a headmaster is, she or he must make lots of decisions, knowing that some will be wrong and with others the outcomes are simply not going to certain for quite a while. The key is to develop some sort efficient process for making decisions, not starting an uncomfortable, awkward process every time a new issue arises.

The Keys Habits of a Successful Decider

Jim and I tried to focus on the conduct of successful heads of school, ones who are both decisive and effective. Here are some tips for decision-making that can be a helpful guide:

Test your judgment: In the pre-decision process, test your thinking/ideas/decisions with a variety of others (depending on the issue) before going forward.

Establish a time frame for a decision: Know when this decision needs to be made and why. Manage backwards.

Own Your Reasoning: Whatever the advice of others, make your decision based on criteria and reasoning that you can “own” and can articulate comfortably. (Further, before the decision is announced get back to those people from the pre-meetings who expressed disagreement.)

Prepare for the Possibilities: Consider the possibility pre-decision that a decision/course of action will prove to be wrong and think through how to handle the consequences.

Listen, and Respond: Once the decision is rolled out, be fully prepared to deal with (i.e. clarify, explain, make more decisions around) its consequences and outcomes. Hiding from tough conversations is a mistake. When they occur, avoid aggressive defensiveness. Instead, stay neutral at first, listen, but offer pro-active explanations to assure the decision has the best chance for calming emotions and muting negative reactions.

Don’t Leave People in the Dark: In the event that, before being finalized, a decision must be delayed or dragged out beyond the optimal time frame, offer periodic updates to those who are awaiting the decision so that the reasons for the delay are clear and understood.

Address Disappointment or Surprise Head On: When a significant decision is firmly made, seek to communicate with those most affected by, most concerned about, most likely to be unhappy with the final choice. You dislike being blindsided and so does everyone else. Determining ahead of time who might feel blindsided—understandably or not—is an important part of a decision-making process, as is determining how to manage such an impact. Leaders with good judgment really think through the various communication aspects all along the decision path.

Acknowledge Your Mistakes and Cut Your Losses: Finally—if there is a “finally” in this area—a decision might take quite a while to reveal its success, problems, or likelihood to fail. As this process plays out, and it could take months, if not years to do so, a head of school must be ready to admit to her or himself that a decision did not work out successfully, particularly as that reality is becoming apparent. Being sure to find the best path between impatience and cutting one’s losses too soon, a successful leader must be ready to say without defensiveness that the decision was wrong and that you are sorry the decision did not work out. Such candor and openness comprise a powerful example of good judgment and sensitivity to those involved in the issues.

People know that decisions do not always work out, but they also sense how hard it can be to take responsibility in such cases. In fact, it does not happen often enough in any leadership position. And admitting to failure or a mistake does not always need a public announcement, but the right people or groups need the school leader to say it. Sometimes the best and most important decisions a headmaster can make is knowing when and how to change course, admit a decision’s failure, to know whom to talk with about it, and then move forward. Preserving your decision-making confidence with your constituents can be a key priority, and only by

being decisive and exercising good judgment in doing so can that confidence be gained.